Stephen J. Cloobeck joins Rabbi Yoshi for a wide-ranging conversation about business, identity, and public service. Best known as the founder and former CEO of Diamond Resorts, Cloobeck reflects on his Jewish upbringing at Stephen Wise Temple, the influence of his father, and how those early experiences continue to shape his values.

They discuss his new book, Facing Hard Truths. Cloobeck also shares why he’s decided to enter the political arena as a candidate for Governor of California in the 2026 election.

This episode explores how personal history, faith, and ambition intersect—and what it means to lead with conviction in uncertain times.